Spend a Peak-Perfect Autumn Weekend in The Catskills

New Yorkers! Do you need a fresh Catskills travel itinerary? Whether you are new to the area or are a seasoned visitor looking for a crop of ideas, this list of places to eat, drink, and breathe in the fresh air will do you some good.

CATSKILLS, NY — An 1872article from The New York Times described the Catskills as having “a delicious sense of remoteness; a feeling of the completeness of nature’s most bountiful gifts of expression.” As it turns out, the sentiment still rings true. This mountainous swath of land, in all its 6,000-square-mile glory, offers the kind of respite city dwellers fantasize about: waterfall hikes, quaint diners, vintage boutiques, and an all-around sense of remote small town life in the best way possible. The Catskills are an idyllic autumn weekend destination. Pack your flannels and hiking boots, folks.

Where to Stay

A good way to know what a place is all about is by looking at the type of accommodations it offers. To sum up the sort of properties found here, the words rustic, cozy, and soulful come to mind.

Historic

One of the perks of visiting a historic region are the storied accommodations — essentially all hotels in the Catskills have had previous lives. Glen Falls House is a boutique hotel in Round Top that was originally built in 1881 as a farmstead and converted into a hotel in the ‘40s. Enjoy waterfall hikes that surround the property or relax by the outdoor fire pit with a bite from their on-property restaurant Trotwood. Head to Seminary Hill Orchard & Cidery, a boarding house and tasting room listed on the National Registry of Historic Places in Callicoon that has eight separate apartment units designed and renovated with Shaker design elements. If you want to get a feel for the Catskills’ Borscht Belt heyday (an era in which the region catered to the Jewish community with resorts, hotels, and camps), Callicoon Hills is a good pick. The century-old resort is worth a stay for the pool alone, but the restaurant, bar, and cute barn don’t hurt, either.

Design-Forward

If you’ve been a trendy hotelier in the last decade, there’s a strong chance you’ve toyed with the idea of opening something in the Catskills. There are seemingly countless boutique properties with strong design points of view, each with their unique spin. Take Spruceton Inn, for example, a nine-room bed and breakfast that oozes rustic minimalism. The accommodations at Urban Cowboy have in-room pot belly stoves, claw foot tubs, and custom hand-printed wallpaper. The DeBruce in the Willowemoc Valley is a historic hotel with mystical mountain views as well as fly fishing and hiking trails, along with daily breakfast and dinner included in your stay.

Glamp-y

If you’ve yet to join the cabin bandwagon, the Catskills are a great place to make that happen. At Piaule in Catskill, you can stay in a "floating" cabin with floor-to-ceiling windows that reveal a sea of trees. (Piaule also has a spa and restaurant.) At Scandinavian-inspired Eastwind, the freestanding Lushna Suite awaits with a deck, private fire pit, outdoor shower, and hammock. If you want something even more outdoorsy, book out a canvas tent at Treetopia campground.

Autumnal Activities

A fall jaunt to the Catskills is unparalleled, courtesy of seasonal activities that are sure to solidify a festive attitude.

Farm Visits

Head to a local farm for apple or pumpkin picking or just to enjoy the fruits of the region. Hurd's Family Farm in Modena is great for apple picking varieties from Granny Smith and Pink Lady to Crispin and Cameo. At Echo Orchard & Farm, you can visit the farm stand situated on 30 acres alongside the West Branch of the Delaware River. For both an apple and pumpkin picking situation, head to Boehm Farm, and don't leave without their cider donuts.

Take a Hike

The main draw of a place like the Catskills is the opportunity to be in nature. Autumn is a particularly magical time of year to hike around golden trees in crisp temperatures. Kaaterskill Falls is a beautiful trail — it's one of the most popular hikes in the area for good reason. If you’re searching for something a bit more private but just as stunning, go to Newman’s Ledge or Overlook Mountain. If little hikers are tagging along, Windham Path is a family-friendly, crowd-pleasing option with picturesque scenery (meandering woodlands and meadows) and manageable terrain.

Leaf Peeping

There’s nothing quite as spectacular as the shades of red, orange, and yellow on leaves in peak autumn. Of course, hiking is a great way to get your leaf peeping fix, but for something even more adventurous, New York Zipline Canopy Tours at Hunter Mountain have aerial platforms, rope bridges, and one of the longest zip line in the world, with a 4.6-mile glide 600 feet above ground.

Cider Tasting

Don't leave without tasting the bounty of the apple orchard in all its forms. A few places to get you started: Awestruck Ciders, Roscoe Beer Company, Arrowood Farms (which also has adorable chickens running around the grounds), and West Kill Brewing.

Where to Eat and Drink

Obviously, a good meal is a perennial requirement for any good trip, but in autumn, cozy flavors and warm dishes feel all the more appealing. Depending on your mood, there are a few directions to go in.

Diners

It really doesn't get much more classic than a throwback, feel-good greasy spoon. Phoenicia Diner is a worthy pit stop, especially for the buckwheat pancakes and Arnold Bennett Skillet. Dixon Roadside and Rosalino's Diner (formerly Woody's) are other solid options.

Fine Dining

Fine dining and the great outdoors may seem like contradictions, but the chefs in this area are doing it the right way — working with local ingredients and hosting meals in rustic, cozy settings. At Cucina, chefs Gianni Scappin and Lois Freedman serve simple, elegant Italian cuisine in a farmhouse setting. Prospect at Scribner's Lodge gives visitors views of Hunter Mountain as they feast on specialities like honeynut squash carbonara.

Farm to Table

Local 111 is a 39-seat restaurant within a preserved gas station run by chef Josephine Proul. Over in Rhinebeck, Peekamoose Restaurant & Tap Room offers a daily changing menu in collaboration with local farmers, vendors, and craft brewers. If you’re in the mood for artisanal pizza, look no further than The Laundrette's wood-fired slices and seasonal menus.

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